Hydrochloric Acid → 6-nitro-7-(3-chloro-4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dione

HRID 1488968

Reaktionsgleichung

Reaktionsgleichung von HRID 1488968
F[C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[Cl:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[OH:24].[OH-].[K+].Cl>CS(C)=O>[N+:14]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:20]1[CH:21]=[CH:22][C:23](=[O:24])[C:18]([Cl:17])=[CH:19]1)[NH:9][C:8](=[O:12])[C:7](=[O:13])[NH:6]2)([O-:16])=[O:15]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 99912306-Fluoro-7-nitro-1,4-dihydroquinoxaline-2,3-dioneHCID 178516476HCID 178516476, Verbindung

Produkt 1

HCID 229035786-nitro-7-(3-chloro-4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dioneAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

First, 267 mg of 7-fluoro-6-nitro-1,4-dihydroquinoxaline-2,3-dione, 171 mg of 3-chloro-4-hydroxypyridine, and 92 mg of powdered potassium hydroxide were added to 3 ml of dry dimethylsulfoxide. The mixture was allowed to react at 130° C. for 80 minutes in a nitrogen atmosphere. Ice water and 4N hydrochloric acid were then added to the reaction mixture so as to adjust its pH to about 2. The resultant yellow precipitate was filtered and washed with water. The precipitate was recrystallized with a mixture of dimethylformaldehyde and water to give 376 mg of yellowish white 6-nitro-7-(3-chloro-4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dione.

Aufarbeitung

  1. customto react at 130° C. for 80 minutes in a nitrogen atmosphere
  2. filtrationThe resultant yellow precipitate was filtered
  3. washwashed with water
  4. customThe precipitate was recrystallized with a mixture of dimethylformaldehyde and water

Quellen und Nachweise

ORD-Eintrag
ord-5942bfa89f5e493e81858f7039df523a
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05677305

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